Issue 36, 2015

Synthesis of norbornane bisether antibiotics via silver-mediated alkylation

Abstract

A small series of norbornane bisether diguanidines have been synthesized and evaluated as antibacterial agents. The key transformation—bisalkylation of norbornane diol 6—was not successful using Williamson methodology but has been accomplished using Ag2O mediated alkylation. Further functionalization to incorporate two guanidinium groups gave rise to a series of structurally rigid cationic amphiphiles; several of which (16d, 16g and 16h) exhibited antibiotic activity. For example, compound 16d was active against a broad range of bacteria including Pseudomonas aeruginosa (MIC = 8 μg mL−1), Escherichia coli (MIC = 8 μg mL−1) and methicillin-resistant Staphylococcus aureus (MIC = 8 μg mL−1).

Graphical abstract: Synthesis of norbornane bisether antibiotics via silver-mediated alkylation

Supplementary files

Article information

Article type
Paper
Submitted
23 Feb 2015
Accepted
16 Mar 2015
First published
16 Mar 2015
This article is Open Access
Creative Commons BY license

RSC Adv., 2015,5, 28582-28596

Author version available

Synthesis of norbornane bisether antibiotics via silver-mediated alkylation

S. M. Hickey, T. D. Ashton, J. M. White, J. Li, R. L. Nation, H. Y. Yu, A. G. Elliott, M. S. Butler, J. X. Huang, M. A. Cooper and F. M. Pfeffer, RSC Adv., 2015, 5, 28582 DOI: 10.1039/C5RA03321G

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